HU214873B - Eljárás glikozidok és ezeket tartalmazó gyógyszerkészítmények előállítására - Google Patents

Eljárás glikozidok és ezeket tartalmazó gyógyszerkészítmények előállítására Download PDF

Info

Publication number: HU214873B
Authority: HU; Hungary
Prior art keywords: glycosides; preparation; derivative; cholestene; ene
Prior art date: 1990-01-23

Application number

HU9202121A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT61778A (en

HU9202121D0 (en

Inventor

Rudolf Erich Klemke

Original Assignee

Rudolf Erich Klemke

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-01-23

Filing date

1991-01-22

Publication date

1998-07-28

1991-01-22 Application filed by Rudolf Erich Klemke filed Critical Rudolf Erich Klemke

1992-12-28 Publication of HU9202121D0 publication Critical patent/HU9202121D0/hu

1993-03-01 Publication of HUT61778A publication Critical patent/HUT61778A/hu

1998-07-28 Publication of HU214873B publication Critical patent/HU214873B/hu

Links

238000000034 method Methods 0.000 title claims abstract description 30
229930182470 glycoside Natural products 0.000 title claims abstract description 15
230000008569 process Effects 0.000 title claims description 25
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
150000002338 glycosides Chemical class 0.000 title abstract description 13
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PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims description 18
-1 lithium aluminum hydride Chemical group 0.000 claims description 13
239000004480 active ingredient Substances 0.000 claims description 9
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239000001257 hydrogen Substances 0.000 claims description 7
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239000007858 starting material Substances 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
BCEIUDAMUFAQMG-UHFFFAOYSA-M CC(C)(C)O[Cr](O)(=O)=O Chemical group CC(C)(C)O[Cr](O)(=O)=O BCEIUDAMUFAQMG-UHFFFAOYSA-M 0.000 claims description 4
150000002303 glucose derivatives Chemical class 0.000 claims description 4
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LLPWGHLVUPBSLP-UTUOFQBUSA-N [(2r,3s,4r)-3,4-diacetyloxy-3,4-dihydro-2h-pyran-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1OC=C[C@@H](OC(C)=O)[C@@H]1OC(C)=O LLPWGHLVUPBSLP-UTUOFQBUSA-N 0.000 claims description 2
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DTGDZMYNKLTSKC-HKQCOZBKSA-N cholest-5-ene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 DTGDZMYNKLTSKC-HKQCOZBKSA-N 0.000 claims 1
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230000008898 degenerative modification Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
229960003654 desoxycortone Drugs 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010218 electron microscopic analysis Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000003925 fat Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
208000013403 hyperactivity Diseases 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
230000010189 intracellular transport Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000011005 laboratory method Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
YQNQTEBHHUSESQ-UHFFFAOYSA-N lithium aluminate Chemical compound [Li+].[O-][Al]=O YQNQTEBHHUSESQ-UHFFFAOYSA-N 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000012907 medicinal substance Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229960003387 progesterone Drugs 0.000 description 1
239000000186 progesterone Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
210000001082 somatic cell Anatomy 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
239000010902 straw Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Saccharide Compounds (AREA)

HU9202121A 1990-01-23 1991-01-22 Eljárás glikozidok és ezeket tartalmazó gyógyszerkészítmények előállítására HU214873B (hu)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4001895A DE4001895A1 (de)	1990-01-23	1990-01-23	Herstellung von insbesondere steroidglykosiden

Publications (3)

Publication Number	Publication Date
HU9202121D0 HU9202121D0 (en)	1992-12-28
HUT61778A HUT61778A (en)	1993-03-01
HU214873B true HU214873B (hu)	1998-07-28

Family

ID=6398603

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU9202121A HU214873B (hu)	1990-01-23	1991-01-22	Eljárás glikozidok és ezeket tartalmazó gyógyszerkészítmények előállítására

Country Status (12)

Country	Link
US (1)	US5278296A (fr)
EP (1)	EP0594581B1 (fr)
JP (2)	JP2612123B2 (fr)
KR (1)	KR100192005B1 (fr)
CN (1)	CN1050365C (fr)
AT (1)	ATE167868T1 (fr)
AU (1)	AU7148991A (fr)
CA (1)	CA2073692A1 (fr)
DE (2)	DE4001895A1 (fr)
HU (1)	HU214873B (fr)
IL (1)	IL96982A (fr)
WO (1)	WO1991011452A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5496806A (en) *	1990-01-23	1996-03-05	R. Erich Klemke	Glycoside compounds and production and use thereof
US5693767A (en) *	1991-01-22	1997-12-02	Harrier Inc.	Glycoside derivatives of acetaminophen
IL102566A0 (en) *	1991-07-22	1993-01-14	Harrier Inc	Glycoside compounds and production and use thereof
US5677286A (en) *	1995-04-27	1997-10-14	The University Of Michigan	Glycosylated analogs of camptothecin
KR0169536B1 (ko) *	1996-02-27	1999-01-15	손경식	신규한 인삼 사포닌, 그의 제조방법 및 이를 유효성분으로 하는 항종양제
US6103884A (en) *	1996-03-27	2000-08-15	The University Of Michigan	Glycosylated analogs of fusidic acid
CN1064048C (zh) *	1996-08-29	2001-04-04	中国科学院昆明植物研究所	青阳参甙丙至甙庚五个化合物及其制备方法和应用
EP1742636B1 (fr) *	2004-05-05	2013-04-10	Immunopharm Aktiengesellschaft	Preparation pour le traitement du cancer
FR2953154B1 (fr) *	2009-11-30	2013-07-12	Rhodia Operations	Procede de preparation d'un catalyseur de deperoxydation
US8921533B2 (en)	2011-07-25	2014-12-30	Chromatin Technologies	Glycosylated valproic acid analogs and uses thereof
WO2020097600A1 (fr) *	2018-11-09	2020-05-14	Rmd Sciences Inc.	Compositions pour le traitement du cancer et d'autres pathologies
KR102141656B1 (ko)	2019-07-16	2020-08-05	선문대학교 산학협력단	글루코실트랜스퍼라제를 이용한 코르티코스테론의 생물 전환 방법 및 이로부터 얻어진 코르티코스테론 글루코시드
CN119143829B (zh) *	2024-11-06	2025-01-28	山东省食品药品检验研究院	一种c21甾体皂苷及其制备方法、应用

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI46067C (fi) *	1968-04-06	1972-12-11	Hoechst Ag	Menetelmä digitoksigeniiniglykosidien valmistamiseksi.
US3857832A (en) *	1972-03-21	1974-12-31	Warner Lambert Co	Process for the preparation of cardiotonic glycosides
US3859047A (en) *	1973-05-29	1975-01-07	Hoffmann La Roche	Standard for serum cholesterol determination
DE2523284B2 (de) *	1975-05-26	1977-03-24	Nippon Shiny aku Co., Ltd., Kyoto (Japan)	Haemostatische, gefaesstabilisierende und antischockmittel
GB1553540A (en) *	1977-02-23	1979-09-26	Green Cross Corp	Medicaments containing cholesterol derivatives
JPS56113799A (en) *	1980-02-08	1981-09-07	Nippon Shinyaku Co Ltd	Glucoside derivative
DE3127933A1 (de) *	1980-07-18	1982-04-08	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von (delta)- oder (beta)-o-glycosyimidaten
US4415731A (en) *	1981-03-30	1983-11-15	Merck & Co., Inc.	Process for the preparation of methyl 2,6-dideoxy-α-D-arabino-hexopyranoside
US4629768A (en) *	1986-05-02	1986-12-16	Olin Corporation	Thermally stable polyurethane elastomers containing glycoside polyols and a method of producing them

1990
- 1990-01-23 DE DE4001895A patent/DE4001895A1/de not_active Withdrawn
1991
- 1991-01-21 IL IL9698291A patent/IL96982A/en not_active IP Right Cessation
- 1991-01-22 CA CA002073692A patent/CA2073692A1/fr not_active Abandoned
- 1991-01-22 WO PCT/EP1991/000115 patent/WO1991011452A1/fr not_active Ceased
- 1991-01-22 HU HU9202121A patent/HU214873B/hu not_active IP Right Cessation
- 1991-01-22 EP EP91902953A patent/EP0594581B1/fr not_active Expired - Lifetime
- 1991-01-22 DE DE69129700T patent/DE69129700T2/de not_active Expired - Fee Related
- 1991-01-22 US US07/644,002 patent/US5278296A/en not_active Expired - Lifetime
- 1991-01-22 CN CN91100394A patent/CN1050365C/zh not_active Expired - Fee Related
- 1991-01-22 JP JP3503078A patent/JP2612123B2/ja not_active Expired - Lifetime
- 1991-01-22 AT AT91902953T patent/ATE167868T1/de not_active IP Right Cessation
- 1991-01-22 AU AU71489/91A patent/AU7148991A/en not_active Abandoned
1992
- 1992-07-22 KR KR1019920701739A patent/KR100192005B1/ko not_active Expired - Fee Related
1995
- 1995-07-18 JP JP7181812A patent/JP2636208B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPH08109192A (ja)	1996-04-30
WO1991011452A1 (fr)	1991-08-08
DE4001895A1 (de)	1991-07-25
US5278296A (en)	1994-01-11
ATE167868T1 (de)	1998-07-15
HUT61778A (en)	1993-03-01
IL96982A (en)	1996-01-31
JP2612123B2 (ja)	1997-05-21
EP0594581A1 (fr)	1994-05-04
DE69129700T2 (de)	1999-02-18
IL96982A0 (en)	1992-03-29
JP2636208B2 (ja)	1997-07-30
JPH05504565A (ja)	1993-07-15
AU7148991A (en)	1991-08-21
EP0594581B1 (fr)	1998-07-01
CN1053239A (zh)	1991-07-24
HU9202121D0 (en)	1992-12-28
KR100192005B1 (en)	1999-06-15
CA2073692A1 (fr)	1991-07-24
DE69129700D1 (de)	1998-08-06
CN1050365C (zh)	2000-03-15

Legal Events

Date	Code	Title	Description
1993-11-29	DGB9	Succession in title of applicant	Owner name: KLEMKE, RUDOLF ERICH, DE
1999-10-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
EP0133995B1 (fr)	1992-04-15	Stéroides et compositions thérapeutiques les contenant
HU214873B (hu)	1998-07-28	Eljárás glikozidok és ezeket tartalmazó gyógyszerkészítmények előállítására
GB1599863A (en)	1981-10-07	Pharmaceutical compositions for use in the inhibition of the biosynthesis of mevalonic acid
EP0310519B1 (fr)	1992-08-19	Nouveaux esters d'acide androstane 17-carboxylique, procédé pour leur préparation et médicament les contenant
US4082780A (en)	1978-04-04	Estradiol derivatives
JP2643943B2 (ja)	1997-08-25	新規な６−もしくは７−メチレンアンドロスタ−１，４−ジエン−３，１７−ジオン誘導体およびその製造方法
EP0210665B1 (fr)	1989-10-18	Steroides utiles comme anti-cancer, anti-obésité, antihyperglycémique, anti-auto-immunitaire et antihypercholestérolémique
US5693767A (en)	1997-12-02	Glycoside derivatives of acetaminophen
Marwah et al.	2001	Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates
EP0443957B1 (fr)	1995-05-10	Nouveaux produits stéroides comportant un radical spiro en position 17, leur procédé de préparation et les intermédiaires de ce procédé, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant
JP2566574B2 (ja)	1996-12-25	抗癌および抗肥満剤として有用なステロイド
US5496806A (en)	1996-03-05	Glycoside compounds and production and use thereof
US5708164A (en)	1998-01-13	Cephalostatin analogues
JPS635097A (ja)	1988-01-11	アンドロスト−４−エン−３，１７−ジオンのメチレン誘導体およびその製造方法
US3655652A (en)	1972-04-11	Aromatically-unsaturated 9alpha-methyl steroids
US3260733A (en)	1966-07-12	1beta-methyl steroids
US3476783A (en)	1969-11-04	6,6-ethylene-9alpha-fluoro steroids
DE1793055C3 (de)	1977-09-08	18 Methyl-1,4-androstadiene, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
KR0154504B1 (ko)	1998-11-16	콜레스테릴 에스테르 전이 단백질 저해제 및 이의 제조방법
JPS63222196A (ja)	1988-09-16	１−メチル−１５α−（１−オキシアルキル）−アンドロスタ−１，４−ジエン−３，１７−ジオン、その製法及びこの化合物を含むエストロゲン生合成抑制剤
Hirschmann et al.	1952	A Partial Synthesis of Δ5-Pregnenetriol-3β, 16α, 20α and of Other 16α-Hydroxysteroids1
JPH07500119A (ja)	1995-01-05	アンドロスト−４−エノ〔４，５−ｂ〕ピロール誘導体およびその製造法
JPH10316700A (ja)	1998-12-02	Ｄ−ホモ−１７−オキサ−１，３，５（１０）−エストラトリエン誘導体
BE851218A (fr)	1977-08-09	Oleandomycines semi-synthetiques antibiotiques
IL42032A (en)	1977-02-28	Delta4 or delta5-androstane (or norandrostane) imidazole benzimidazole and pyrazole carboxylates their preparation and pharmaceutical compositions containing them